McKee: “What really caught my attention in this discussion was the involvement of Lewis Gross, Nylander’s agent. Initially, it seemed like a deal might be on the horizon, with numbers being discussed and expectations being met. However, it appears that the situation might be more complicated than that. The indications suggest they may not be looking for a straightforward agreement, but rather considering the option of entering free agency instead.

Bourne: “If they’re going to overpay you, sure, you might sign, but otherwise, many of Lewis Gross’s clients tend to explore the free agency market.”

McKee: “It’s interesting to see how many players like Brandon Saad, Krug, Dumoulin, and Noel Acciari have opted to leave their former teams rather than re-sign, which raises questions about Nylander’s situation.”

Kypreos: “They’ve faced similar issues before. Although he was a restricted free agent then, it still resulted in a lengthy negotiation process that delayed his start to the season. They know they are dealing with an agent who is comfortable pushing negotiations to the very last moment.”

Bourne: “Exactly.”

Kypreos: “Now, the question is, will they wait to see if the Chicago Blackhawks come in with an offer that makes the Leafs reconsider, asking, ‘Do you want to match this?’ Is that the direction this is headed?”

Bourne: “That’s a real possibility. The concerning part, as mentioned in this discussion, is that if Nylander leaves, how will the team manage when it comes time for Mitch Marner’s contract negotiation? Losing both elite wingers would severely impact the team’s roster.”

So, at that point, you face a dilemma: keep one of your top players, your game-changer, or risk losing them both.”

Kypreos: “Do you make a choice now, or do you wait?”

Bourne: “That’s the challenge.”

Kypreos: “Or do you find a way to retain both players?”

Bourne: “It’s a critical decision. You either make a choice now or offer Nylander the additional $500,000 he’s seeking.”

Kypreos: “Do you see any scenario where they consider trading him in March?”

Bourne: “Willy? I don’t think so.”

Bourne: “The only reason I might say yes is that Brad Treliving has made it clear he wants to avoid a situation similar to what happened with Johnny Gaudreau, where he lost a player without being able to make any moves.”

McKee: “It’s striking how similar this situation is, with a top-tier player considering a move from one scenario to another, especially since they share the same agent.”

Bourne: “That’s correct. Lewis Gross.”

McKee: “Lewis Gross. It feels like a case of déjà vu here, as if we’re reliving the same scenario.”